This proposal concerns the synthesis of the structurally novel antitumor antibiotic, quinocarcin. In addition to its significant activity against mouse lymphocytic leukemia P388, quinocarcin shares several structural features with the saframycins, renieramycins and safracins. The development of an efficient synthetic route to quinocarcin will not only provide access to quinocarcin and it derivatives, but will also facilitate future synthetic approaches to these other, more complex, compounds of significant biomedical interest. The absolute stereochemistry of quinocarcin is unknown; the synthesis proposed here will allow the determination of the absolute configuration of quinocarcin. The total synthesis will provide the means to produce similar compounds for biological study. The chemistry proposed here is an appropriate combination of both old and new science. A relatively straightforward approach to the tetrahydroisoquinoline portion of quinocarcin will allow new chemistry to be explored to provide a route to the synthetically challenging CD rings of the compound, and thus provide useful chemical technology for the syntheses of related compounds of medicinal interest. Specifically, the use of a model system for the tetrahydroisoquinoline ring system will allow the early commencement of work on the more difficult portion of the molecule; the proposed model will not differ significantly enough to affect the chemistry used to design a synthesis for the remainder of the molecule. While work is underway using the model system, concurrent work can then explore the most efficient and stereocontrolled route to the tetrahydroisoquinoline portion of the molecule.